27 Osborn Road
Sherman, Connecticut 06784
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,540
- Acres
- 7.71
- Year Built
- 2012
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
This impeccable 4 bedroom home is sited on 7.7 private acres w/four fenced paddocks and a 3/4 stall stable for horses at the end of a quiet country lane.The home has a sought after open floor plan on the 1st level. The large, eat-in kitchen has a vast granite center island & includes a 6 burner/two oven range w/egress to the outdoor stone terrace. The open flow to the family room and dining room is ideal for today's lifestyle. The family room features built-ins & an Extraordinaire Fireplace capable of heating the entire home! It is back to back with the outdoor fireplace on the expansive stone terrace. A convenient first floor bedroom with a newly renovated full bath can also be used as a gym, office or library. There is an additional room at that end of the home that is perfect for a home office, den or music room. The upper level has 3 bedrooms including the primary ensuite bedroom w/3 walk-in closets. There is a hall bath for the other two bedrooms to share. The walk-out lower level/basement has high ceilings & a poured concrete foundation. The beautifully appointed 4 stall/3 stalls plus tack room, center aisle stable has large stalls with a stone aisle. The stalls have rubber matting & the 4 fenced paddocks are all adjacent to the barn. There is a fenced round pen as well as access to the Naromi trail system. The in-ground pool is heated and fenced with lovely gardens surrounding it. A charming, in character garage/storage building graces the property as well.
Key Facts
- City/Town
- Sherman
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2012
- Days on Market
- 136 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 3,540 sq ft
- Lot Size
- 7.71 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $9,225 / Annually
Market Snapshot
The Sherman Market
Single Family · trailing 12 months
Active Listings
28
4 under contract
Median List Price
$1.05M
28 active listings
Median Closed Price
$675,000
43 sales
Median Days on Market
63
28 active listings
Median $ / Sq Ft
$340
28 active listings
Sale-to-List Ratio
96.5%
43 sales
How this home compares
List Price
$1.59M
vs $1.05M median
51.9% above median
Price / Sq Ft
$451
vs $340 median
32.6% above median
Days on Market
136 days
vs 63 days median
73 days longer than median
Based on 28 active and 43 closed sales (trailing 12 mo) of single family in Sherman. Source: SmartMLS · As of July 30, 2026.
Location
27 Osborn Road, Sherman, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$8,132
- Property Taxes$769
- Insurance$532
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Sherman
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2012
- New Construction
- No/Resale
- Living Area
- 3,540 sq ft
Schools
- Elementary
- Sherman
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hydro Air
- Heat Fuel
- Propane
- Cooling
- Central AirZoned
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- Near the mudroom & garage
- Appliances
- Gas CooktopOven/RangeMicrowaveRefrigeratorFreezerDishwasherWasherDryer
- Basement
- FullFull With Walk-Out
- In-Law Apartment
- No
- Interior Features
- Auto Garage Door OpenerOpen Floor PlanSecurity System
- Additional Rooms
- FoyerLaundry RoomMusic Room
Exterior & Lot
- Lot Size
- 7.71 acres
- Zoning
- Residential
- Garage / Parking
- 3 garage spacesAttached GarageDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- HeatedSafety FenceSalt WaterIn Ground Pool
- Construction
- Clapboard
- Color
- Beige
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- TerraceBarnDeckGarden AreaStablePaddock
- Lot Description
- Professionally Landscaped
Listing & Financials
- Property Taxes
- $9,225 / Annually
- Days on Market
- 136
- MLS #
- 24159584
- MLS Status
- Active
Similar Properties
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Co-Listed By
Robyn Bonder
Douglas Elliman of Connecticut
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/30/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/30/2026 at 7:40 PM UTC.